Starting with cholic acid, the synthesis of simaroubaceous alpha- lactone analogs of holacanthone and quassin having potential antineoplastic properties are outlined. Sequencing the method of Barbier-Wieland which gives 3 alpha, 7 alpha, 12 alpha-triacetoxy-20- oxo-5B-pregnane with direct bromination of the 17 alpha-position, subsequent elimination to the 16-ene, and then oxidation with chromic acid gives the corresponding 16, 17-seco-16, 17-dioic acid. Further elaboration of this product yields an alpha-lactone analog of quassin. Integrated with this pursuit are Claisen and Simmons-Smith studies aimed at incorporating an 8 Beta-methyl or 8 Beta-hydroxymethyl group onto the steroid and D-secosteroid systems.